Toluene → 4-(2,3,4-Trimethoxy-6-methylbenzoyl)-2-chloro-3-trifluoromethyl-5-methoxypyridine

HRID 1835420Notes

Reaction equation

HRID 1835420 reaction equation
P(Cl)(Cl)([Cl:3])=O.C1(C)C=CC=CC=1.[CH3:13][O:14][C:15]1[C:35]([O:36][CH3:37])=[C:34]([O:38][CH3:39])[CH:33]=[C:32]([CH3:40])[C:16]=1[C:17]([C:19]1[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][N+:22]([O-])=[CH:21][C:20]=1[O:30][CH3:31])=[O:18]>CN(C)C=O>[CH3:13][O:14][C:15]1[C:35]([O:36][CH3:37])=[C:34]([O:38][CH3:39])[CH:33]=[C:32]([CH3:40])[C:16]=1[C:17]([C:19]1[C:20]([O:30][CH3:31])=[CH:21][N:22]=[C:23]([Cl:3])[C:24]=1[C:25]([F:28])([F:27])[F:26])=[O:18]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 121513054-(2,3,4-trimethoxy-6-methylbenzoyl)-3-methoxy-5-trifluoromethylpyridine-N-oxide

Product 1

HCID 121514224-(2,3,4-Trimethoxy-6-methylbenzoyl)-2-chloro-3-trifluoromethyl-5-methoxypyridineYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.8 ml (19 mmol) of phosphorus oxychloride was added to 4 ml of toluene and 8 ml of dimethylformamide at 0° C., followed by stirring for 10 minutes, and 4.0 g (10 mmol) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-methoxy-5-trifluoromethylpyridine-N-oxide was added thereto, followed by stirring for 20 minutes. Stirring was carried out at room temperature for 2 hours, and then the reaction solution was poured into ice water to terminate the reaction. The aqueous layer was extracted with ethyl acetate, and then the organic layer was dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 3.57 g (yield 85%) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2-chloro-3-trifluoromethyl-5-methoxypyridine (compound No. 123; m.p. 117-119° C.).

Workup

  1. stirringby stirring for 20 minutes
  2. stirringStirring
  3. waitwas carried out at room temperature for 2 hours
  4. customto terminate
  5. customthe reaction
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  8. filtrationsubjected to filtration
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe crude product thus obtained
  11. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-46bb9b8d05514d8c893e70c7d20db125
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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